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Azide–Alkyne 1,3-Dipolar Cycloadditions: a Valuable Tool in Carbohydrate Chemistry

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Heterocycles from Carbohydrate Precursors

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 7))

Abstract

Recent applications of the 1,3-dipolar cycloaddition reaction of azides and alkynes in carbohydrate chemistry are summarized in the present review. The efficient catalyzed version of this reaction, also referred to as one of the so-called click chemistry reactions, has joined in a short period of time a select group of the most efficient and useful organic reactions. In particular, its application in the carbohydrate field has shown its value as a synthetic tool allowing the preparation of a wide range of carbohydrate-containing molecular constructs such as glycopeptides, glycoaminoacids, glycoclusters, glycodendrimers, glycopolymers, glycosylated biomolecules, and immobilization of carbohydrates onto solid surfaces (glycoarrays) as the most representative examples. In the majority of cases, the formed 1,2,3-triazole heterocycle plays the role of a linking tether between the coupling partners.

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References

  1. Padwa A, Pearson WH (2003) Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products. Wiley, Chichester, UK

    Google Scholar 

  2. Gallos JK, Koumbis AE (2003) Curr Org Chem 7:397

    Article  CAS  Google Scholar 

  3. Koumbis AE, Gallos JK (2003) Curr Org Chem 7:585

    Article  CAS  Google Scholar 

  4. Koumbis AE, Gallos JK (2003) Curr Org Chem 7:771

    Article  CAS  Google Scholar 

  5. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed Engl 41:2596

    Article  CAS  Google Scholar 

  6. Tornoe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057

    Article  CAS  Google Scholar 

  7. Kolb HC, Sharpless KB (2003) Drug Discov Today 8:1128

    Article  CAS  Google Scholar 

  8. Wang Q, Chittaboina S, Barnhill HN (2005) Lett Org Chem 2:293

    Article  CAS  Google Scholar 

  9. Mock WL, Irra TA, Wepsiec JP, Adhya M (1989) J Org Chem 54:5302

    Article  CAS  Google Scholar 

  10. Chen J, Rebek J (2002) Org Lett 4:327

    Article  CAS  Google Scholar 

  11. Howell SJ, Spencer N, Philp D (2001) Tetrahedron 57:4945

    Article  CAS  Google Scholar 

  12. Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2005

    Google Scholar 

  13. Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV (2005) J Am Chem Soc 127:210

    Article  CAS  Google Scholar 

  14. Bock VD, Hiemstra H, van Maarseveen JH (2006) Eur J Org Chem 51:68

    Google Scholar 

  15. Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG (2003) J Am Chem Soc 125:3192

    Article  CAS  Google Scholar 

  16. Speers AE, Adam GC, Cravatt BF (2003) J Am Chem Soc 125:4686

    Article  CAS  Google Scholar 

  17. Chan TR, Hilgraf R, Sharpless KB, Fokin VV (2004) Org Lett 6:2853

    Article  CAS  Google Scholar 

  18. Meng JC, Fokin VV, Finn MG (2005) Tetrahedron Lett 46:4543

    Article  CAS  Google Scholar 

  19. Lewis WG, Magallon FG, Fokin VV, Finn MG (2004) J Am Chem Soc 126:9152

    Article  CAS  Google Scholar 

  20. Perez-Balderas F, Ortega-Muñoz M, Morales-Sanfrutos J, Hernandez-Mateo F, Calvo-Flores FG, Calvo-Asin JA, Isac-Garcia J, Santoyo-Gonzalez F (2003) Org Lett 5:1951

    Article  CAS  Google Scholar 

  21. Girard C, Onen E, Aufort M, Beauviere S, Samson E, Herscovici J (2006) Org Lett 8:1689

    Article  CAS  Google Scholar 

  22. Orgueira HA, Fokas D, Isome Y, Chan PCM, Baldino CM (2005) Tetrahedron Lett 46:2911

    Article  CAS  Google Scholar 

  23. Pachon LD, van Maarseveen JH, Rothenberg G (2005) Adv Syn Cat 347:811

    Article  CAS  Google Scholar 

  24. Chittaboina S, Xie F, Wang Q (2005) Tetrahedron Lett 46:2331

    Article  CAS  Google Scholar 

  25. Lober S, Rodriguez-Loaiza P, Gmeiner P (2003) Org Lett 5:1753

    Article  CAS  Google Scholar 

  26. Lober S, Gmeiner P (2004) Tetrahedron 60:8699

    Article  CAS  Google Scholar 

  27. Collman JP, Devaraj NK, Chidsey CED (2004) Langmuir 20:1051

    Article  CAS  Google Scholar 

  28. Kuijpers BHM, Groothuys S, Keereweer AR, Quaedflieg PJLM, Blaauw RH, vanDelft FL, Rutjes FPJT (2004) Org Lett 6:3123

    Article  CAS  Google Scholar 

  29. Dondoni A, Giovannini PP, Massi A (2004) Org Lett 6:2929

    Article  CAS  Google Scholar 

  30. Giguere D, Patnam R, Bellefleur MA, St-Pierre C, Sato S, Roy R (2006) Chem Commun 2379

    Google Scholar 

  31. Macmillan D, Blanc J (2006) Org Biomol Chem 4:2847

    Article  CAS  Google Scholar 

  32. Ermolat'ev D, Dehaen W, Van der Eycken E (2004) QSAR Comb Sci 23:915

    Article  CAS  Google Scholar 

  33. Hotha S, Kashyap S (2006) J Org Chem 71:364

    Article  CAS  Google Scholar 

  34. Arosio D, Bertoli M, Manzoni L, Scolastico C (2006) Tetrahedron Lett 47:3697

    Article  CAS  Google Scholar 

  35. Salameh BA, Leffler H, Nilsson UJ (2005) Bioorg Med Chem Lett 15:3344

    Article  CAS  Google Scholar 

  36. Tejler J, Tullberg E, Frejd T, Leffler H, Nilsson UJ (2006) Carbohydr Res 341:1353

    Article  CAS  Google Scholar 

  37. Griffith BR, Langenhan JM, Thorson JS (2005) Curr Opin Biotech 16:622

    Article  CAS  Google Scholar 

  38. Miner PL, Wagner TR, Norris P (2005) Heterocycles 65:1035

    Article  CAS  Google Scholar 

  39. Perez-Balderas F (2005) PhD Thesis. University of Granada

    Google Scholar 

  40. Casas-Solvas JM, Vargas-Berenguel A, Capitan-Vallvey LF, Santoyo-Gonzalez F (2004) Org Lett 21:3687

    Article  CAS  Google Scholar 

  41. Zhu XM, Schmidt RR (2004) J Org Chem 69:1081

    Article  CAS  Google Scholar 

  42. Hager C, Miethchen R, Reinke H (2000) J Fluor Chem 104:135

    Article  CAS  Google Scholar 

  43. IJsselstijn M, Cintrat JC (2006) Tetrahedron 62:3837

    Article  CAS  Google Scholar 

  44. Lee BY, Park SR, Jeon HB, Kim KS (2006) Tetrahedron Lett 47:5105

    Article  CAS  Google Scholar 

  45. Guezguez R, Bougrin K, El Akri K, Benhida R (2006) Tetrahedron Lett 47:4807

    Article  CAS  Google Scholar 

  46. Deng S, Gangadharmath U, Chang CWT (2006) J Org Chem 71:5179

    Article  CAS  Google Scholar 

  47. Roy R (2003) Trends Glycosci Glyc 15:291

    CAS  Google Scholar 

  48. Jayaraman N, Nepogodiev SA, Stoddart JF (1997) Chem Eur J 3:1193

    CAS  Google Scholar 

  49. Bezouska K (2002) Rev Mol Biotechnol 90:269

    Article  CAS  Google Scholar 

  50. Turnbull WB, Stoddart JF (2002) Rev Mol Biotechnol 90:231

    Article  CAS  Google Scholar 

  51. Roy R, Baek M-G (2002) Rev Mol Biotech 90:291

    Article  CAS  Google Scholar 

  52. Ladmiral V, Melia E, Haddleton DM (2004) Eur Polym J 40:431

    Article  CAS  Google Scholar 

  53. Nishikawa M, Kawakami S, Yamashita F, Hashida M (2003) Methods Enzy 373:384

    Article  CAS  Google Scholar 

  54. Thomas JR, Liu X, Hergenrother PJ (2005) J Am Chem Soc 127:12434

    Article  CAS  Google Scholar 

  55. De Oliveira RN, Sinou D, Srivastava RM (2006) Synthesis 467

    Google Scholar 

  56. Malkoch M, Schleicher K, Drockenmuller E, Hawker CJ, Russell TP, Wu P, Fokin VV (2005) Macromolecules 38:3663

    Article  CAS  Google Scholar 

  57. Joosten JAF, Tholen NTH, El Maate FA, Brouwer AJ, van Esse GW, Rijkers DTS, Liskamp RMJ, Pieters RJ (2005) Eur J Org Chem p 3182

    Google Scholar 

  58. Fernandez-Megia E, Correa J, Rodriguez-Meizoso I, Riguera R (2006) Macromolecules 39:2113

    Article  CAS  Google Scholar 

  59. Wu P, Malkoch M, Hunt JN, Vestberg R, Kaltgrad E, Finn MG, Fokin VV, Sharpless KB, Hawker CJ (2005) Chem Commun 5775

    Google Scholar 

  60. Ortega-Munoz M, Lopez-Jaramillo J, Hernandez-Mateo F, Santoyo-Gonzalez F (2006) Adv Synth Cat 348:2410

    Article  CAS  Google Scholar 

  61. Hasegawa T, Umeda M, Numata M, Li C, Bae AH, Fujisawa T, Haraguchi S, Sakurai K, Shinkai S (2005) Carbohydr Res 341:35

    Article  CAS  Google Scholar 

  62. Ladmiral V, Mantovani G, Clarkson GJ, Cauet S, Irwin JL, Haddleton DM (2006) J Am Chem Soc 128:4823

    Article  CAS  Google Scholar 

  63. Malkoch M, Thibault RJ, Drockenmuller E, Messerschmidt M, Voit B, Russell TP, Hawker CJ (2005) J Am Chem Soc 127:14942

    Article  CAS  Google Scholar 

  64. Srinivasachari S, Liu Y, Zhang G, Prevette L, Reineke TM (2006) J Am Chem Soc 128:8176

    Article  CAS  Google Scholar 

  65. Marmuse L, Nepogodiev SA, Field RA (2005) Org Biomol Chem 3:2225

    Article  CAS  Google Scholar 

  66. Bodine KD, Gin DY, Gin MS (2004) J Am Chem Soc 126:1638

    Article  CAS  Google Scholar 

  67. Bodine KD, Gin DY, Gin MS (2005) Org Lett 7:4479

    Article  CAS  Google Scholar 

  68. Billing JF, Nilsson UJ (2005) J Org Chem 70:4847

    Article  CAS  Google Scholar 

  69. Lin H, Walsh CT (2004) J Am Chem Soc 126:13998

    Article  CAS  Google Scholar 

  70. Gupta SS, Kuzelka J, Singh P, Lewis WG, Manchester M, Finn MG (2005) Bioconjugate Chem 16:1572

    Article  CAS  Google Scholar 

  71. Gupta SS, Raja KS, Kaltgrad E, Strable E, Finn MG (2005) Chem Commun 4315

    Google Scholar 

  72. Bouillon C, Meyer A, Vidal S, Jochum A, Chevolot Y, Cloarec JP, Praly JP, Vasseur JJ, Morvan F (2006) J Org Chem 71:4700

    Article  CAS  Google Scholar 

  73. Hassane FS, Frisch B, Schuber F (2006) Bioconjugate Chem 17:849

    Article  CAS  Google Scholar 

  74. Ballell L, Alink KJ, Slijper M, Versluis C, Liskamp RMJ, Pieters RJ (2005) ChemBioChem 6:291

    Article  CAS  Google Scholar 

  75. Wang D (2003) Proteomics 3:2167

    Article  CAS  Google Scholar 

  76. Ortiz MC, Garcia Fernandez JM (2002) ChemBioChem 3:819

    Article  Google Scholar 

  77. Love KR, Seeberger PH (2002) Angew Chem Int Ed 41:3583

    Article  CAS  Google Scholar 

  78. Feizi T, Fazio F, Chai W, Wong CH (2003) Curr Opin Struct Biol 13:637

    Article  CAS  Google Scholar 

  79. Fazio F, Bryan MC, Blixt O, Paulson JC, Wong CH (2002) J Am Chem Soc 124:14397

    Article  CAS  Google Scholar 

  80. Bryan MC, Fazio F, Lee HK, Huang CY, Chang A, Best MD, Calarese DA, Blixt O, Paulson JC, Burton D, Wilson IA, Wong CH (2004) J Am Chem Soc 126:8640

    Article  CAS  Google Scholar 

  81. Huang GL, Liu TC, Liu MX, Mei XY (2005) Anal Biochem 340:52

    Article  CAS  Google Scholar 

  82. Zhang Y, Luo S, Tang Y, Yu L, Hou KY, Cheng JP, Zeng X, Wang PG (2006) Anal Chem 78:2001

    Article  CAS  Google Scholar 

  83. Sun XL, Stabler CL, Cazalis CS, Chaikof EL (2006) Bioconjugate Chem 17:52

    Article  CAS  Google Scholar 

  84. Dolhem F, Al Tahli F, Lievre C, Demailly G (2005) Eur J Org Chem 5019

    Google Scholar 

  85. Flessner T, Wong CH (2000) Tetrahedron Lett 41:7805

    Article  CAS  Google Scholar 

  86. Hotha S, Anegundi RI, Natu AA (2005) Tetrahedron Lett 46:4585

    Article  CAS  Google Scholar 

  87. Ray A, Manoj K, Bhadbhade MM, Mukhopadhyay R, Bhattacharjya A (2006) Tetrahedron Lett 47:2775

    Article  CAS  Google Scholar 

  88. Marco-Contelles J, Rodriguez-Fernadez M (2001) J Org Chem 66:3717

    Article  CAS  Google Scholar 

  89. Hoffmann B, Bernet B, Vasella A (2002) Helv Chim Acta 85:265

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Departamento de Química Orgánica, Instituto de Biotecnología.Facultad de Ciencias, Universidad de Granada, 18071, Granada, Spain

    Francisco Santoyo-González & Fernando Hernández-Mateo

Authors
  1. Francisco Santoyo-González
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  2. Fernando Hernández-Mateo
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Correspondence to Francisco Santoyo-González .

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El Sayed H. El Ashry

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Santoyo-González, F., Hernández-Mateo, F. (2007). Azide–Alkyne 1,3-Dipolar Cycloadditions: a Valuable Tool in Carbohydrate Chemistry. In: El Ashry, E.S.H. (eds) Heterocycles from Carbohydrate Precursors. Topics in Heterocyclic Chemistry, vol 7. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_050

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